Diisopropylethylamine → HCID 86694436, compound

Participants

Reaction Steps

To a solution of 4-[(3aR,7aR)-octahydro-1H-pyrrolo[3,2-b]pyridin-1-yl]-7H-pyrrolo[2,3-d]pyrimidine (12 mg, 0.049 mmol) in acetonitrile (493 tip was added DMAP (9.0 mg, 0.074 mmol) and DIPEA (17 μL, 0.099 mmol) followed by isopropylsulfonyl chloride (12 mg, 0.049 mmol). The reaction mixture was stirred for 20 hours at room temperature before being diluted with 1.0 mL DMSO and purified by mass-triggered reverse-phase HPLC using a Waters X-bridge Prep C18 column (5 micron, 19×100 mm), eluting with an ACN/water gradient (0.1% formic acid as modifier) to afford 4-{(3aR,7aR)-4-[(1-methylethyl)sulfonyl]octahydro-1H-pyrrolo[3,2-b]pyridin-1-yl}-7H-pyrrolo[2,3-d]pyrimidine. LRMS calc'd for C16H24N5O2S [M+H]+, 350.2; found 350.2. 1H NMR (500 MHz, DMSO-D6) δ 11.6 (s, 1H); 8.04 (s, 1H); 7.09 (s, 1H), 6.51 (s, 2H); 4.29 (br s, 2H); 3.97-3.64 (br m, 21-1); 3.53 (d, 2H, J=11Hz); 3.38-3.34 (m, 1H); 3.02 (t, 1H. J=10Hz); 2.01 (br s, 1H); 1.64 (s, 1H), 1.62 (br s, 1H), 1.24-1.54 (br m, 2H). 1.21 (t, 6H, J=5.5Hz). Jak1 activity: ++

Provenance & Evidence